methyl 4-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzoate

ID: ALA4758908

PubChem CID: 162658380

Max Phase: Preclinical

Molecular Formula: C22H25N5O3

Molecular Weight: 407.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(Nc2ncc3cc(C(=O)N(C)C)n(C4CCCC4)c3n2)cc1

Standard InChI:  InChI=1S/C22H25N5O3/c1-26(2)20(28)18-12-15-13-23-22(25-19(15)27(18)17-6-4-5-7-17)24-16-10-8-14(9-11-16)21(29)30-3/h8-13,17H,4-7H2,1-3H3,(H,23,24,25)

Standard InChI Key:  QKUPEYVJRBJWLO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   17.2961  -11.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1211  -11.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3779  -10.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7086  -10.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0435  -10.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7047   -9.2146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2902   -7.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0366   -8.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2524   -8.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6383   -8.4358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8541   -8.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8087   -7.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0822   -9.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1153   -7.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3683   -8.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1722   -8.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7239   -8.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4661   -7.5025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6628   -7.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5310   -8.4591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0826   -7.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8868   -8.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4380   -7.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1825   -6.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3706   -6.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8229   -7.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7331   -6.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5405   -6.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0911   -5.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4764   -5.2206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6 15  1  0
 14  7  1  0
  7  8  2  0
  8  6  1  0
  4  6  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4758908

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 407.47

Molecular Weight (Monoisotopic): 407.1957

AlogP: 3.78

#Rotatable Bonds: 5

Polar Surface Area: 89.35

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.23

CX Basic pKa: 3.74

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -1.19

References

1. Wei M,Zhao R,Cao Y,Wei Y,Li M,Dong Z,Liu Y,Ruan H,Li Y,Cao S,Tang Z,Zhou Y,Song W,Wang Y,Wang J,Yang G,Yang C.  (2021)  First orally bioavailable prodrug of proteolysis targeting chimera (PROTAC) degrades cyclin-dependent kinases 2/4/6 in vivo.,  209  [PMID:33256948] [10.1016/j.ejmech.2020.112903]

Source

Source(1):

• Scientific Literature